Synthesis and self-alkylation of isotope-coded affinity tag reagents

Bioconjugate Chemistry

Volumn 16, Issue 2, 2005, Pages 458-464

  Zhang, Zhidong ^a   Edwards, Patrick J ^a   Roeske, Roger W ^a   Guo, Lili ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CHLORINE COMPOUNDS; COBALT COMPOUNDS; RESINS; SODIUM BOROHYDRIDE; SYNTHESIS (CHEMICAL);

BIOTINYLATIONS; CHLORIDE RESIN; ISOTOPE-CODED AFFINITY TAG; RANEY NICKEL; SODIUM BORO HYDRIDES; SODIUM BOROHYDRIDES; SOLID-PHASE METHOD; SYNTHESISED;

AMINES;

CHLOROTRITYLCHLORIDE RESIN; COBALT CHLORIDE; DEUTERIUM; DIAMINE; N (10 IODOACETAMIDO 2,5,5,6,6,9 HEXADEUTERO 4,7 DIOXA DECANYL)BIOTINAMIDE; N (10 IODOACETAMIDO 4,7 DIOXA DECANYL)BIOTINAMIDE; N (13 IODOACETAMIDO 2,2,3,3,11,11,12,12 OCTADEUTERO 4,7,10 TRIOXA TRIDECANYL)BIOTINAMIDE; N (13 IODOACETAMIDO 4,7,10 TRIOXA TRIDECANYL)BIOTINAMIDE; NICKEL; NITRILE; REAGENT; RESIN; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BIOTINYLATION; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID; SYNTHESIS;

EID: 15244346042     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc049777y     Document Type: Article

References (28)

1. Blackstock, W. P., and Weir, M. P. (1999) Proteomics: quantitative and physical mapping of cellular proteins. Trends Biotechnol. 17, 121-127.
2. Gabor Miklos, G. L., and Maleszka, R. (2001) Integrating molecular medicine with functional proteomics: realities and expectations. Proteomics 1, 30-41.
3. Witzmann, F. A., and Li, J. (2002) Cutting-edge technology. II. Proteomics: core technologies and applications in physiology. Am. J. Physiol. Gastrointest. Liver Physiol. 282, G735-G741.
4. Figeys, D. (2002) Proteomics approaches in drug discovery. Anal. Chem. 74, 412A-419A.
5. Goshe, M. B., and Smith, R. D. (2003) Stable isotope-coded proteomic mass spectrometry. Curr. Opin. Biotechnol. 14, 101-109.
6. Tao, W. A., and Aebersold, R. (2003) Advances in quantitative proteomics via stable isotope tagging and mass spectrometry. Curr. Opin. Biotechnol. 14, 110-118.
7. Gygi, S. P., Rist, B., Gerber, S. A., Turecek, F., Gelb, M. H., and Aebersold, R. (1999) Quantitative analysis of complex protein mixtures using isotope-coded affinity tags. Nat. Biotechnol. 17, 994-999.
8. Zhang, R., Sioma, C. S., Wang, S., and Regnier, F. E. (2001) Fractionation of isotopically labeled peptides in quantitative proteomics. Anal. Chem. 73, 5142-5149.
9. Yu, L. R., Johnson, M. D., Conrads, T. P., Smith, R. D., Morrison, R. S., and Veenstra, T. D. (2002) Proteome analysis of camptothecin-treated cortical neurons using isotope-coded affinity tags. Electrophoresis 23, 1591-1598.
10. Shiio, Y., Donohoe, S., Yi, E. C., Goodlett, D. R., Aebersold, R., and Eisenman, R. N. (2002) Quantitative proteomic analysis of Myc oncoprotein function. EMBO J. 21, 5088-5096.
11. Lee, H., Griffin, T. J., Gygi, S. P., Rist, B., and Aebersold, R. (2002) Development of a multiplexed microcapillary liquid chromatography system for high-throughput proteome analysis. Anal. Chem. 74, 4353-4360.
12. Guina, T., Wu, M., Miller, S. I., Purvine, S. O., Yi, E. C., Eng, J., Goodlett, D. R., Aebersold, R., Ernst, R. K., and Lee, K. A. (2003) Proteomic analysis of Pseudomonas aeruginosa grown under magnesium limitation. J. Am. Soc. Mass Spectrom. 14, 742-751.
13. Oda, Y., Owa, T., Sato, T., Boucher, B., Daniels, S., Yamanaka, H., Shinohara, Y., Yokoi, A., Kuromitsu, J., and Nagasu, T. (2003) Quantitative chemical proteomics for identifying candidate drug targets. Anal. Chem. 75, 2159-2165.
14. Gerber, S. A., Scott, R., Turecek, F., and Gelb, M. H. (1999) Analysis of rates of multiple enzymes in cell lysates by electrospray ionization mass spectrometry. J. Am. Chem. Soc. 121, 1102-1103.
15. Patel, A., and Perrin, D. M. (2004) Efficient synthesis of isotopically pure isotope-coded affinity tagging reagents. Bioconjugate Chem. 15, 224-230.
16. Ashikaga, K., Ito, S., Yamamoto, M., and Nishijima, Y. (1988) Intramolecular end-to-end reactions of photoactive terminal groups linked by poly(oxyethylene) chains. Bull. Chem. Soc. Jpn. 61, 2443-2449.
17. Gerber, S. A., Turecek, F., and Gelb, M. H. (2001) Design and synthesis of substrate and internal standard conjugates for profiling enzyme activity in the sanfilippo syndrome by affinity chromatograghy/electrospray ionization mass spectrometry. Bioconjugate Chem. 12, 603-615.
18. Horner, L. (1969) Competing processes on the surface of Raney nickel during the hydrogenation of olefins. Ann. N.Y. Acad. Sci. 158, 456-470.
19. Hazzard, B. J. (1973) Organicum, Chapter 7, Addison-Wesley Publishing Co., Inc., Reading, MA.
20. Yoon, N. M., and Brown, H. C. (1968) Selective reductions. XII. Explorations in some representative applications of aluminum hydride for selective reductions. J. Am. Chem. Soc. 90, 2927-2938.
21. Brown, H. C., Choi, Y. M., and Narasimhan, S. (1981) Improved procedure for borane-dimethyl sulfide reduction of nitriles. Synthesis 605-606.
22. Satoh, T., Suzuki, S., Suzuki, Y., Miyaji, Y., and Imai, Z. (1969) Reduction of organic compounds with sodium borohydride-transition metal salt systems (1). Reduction of organic nitrile, nitro and amide compounds to primary amines. Tetrahedron Lett. 52, 4555-4558.
23. Heinzman, S. W., and Ganem, B. (1982) The mechanism of sodium borohydride-cobaltous chloride reductions. J. Am. Chem. Soc. 104, 6801-6802.
24. Osby, J. O., Heinzman, S. W., and Ganem, B. (1986) Studies on the mechanism of transition-metal-assisted sodium borohydride and lithium aluminum hydride reductions. J. Am. Chem. Soc. 108, 67-72.
25. Egli, R. A. (1970) Katalysierte Nitrilreduktionen mit natriumborhydrid. Helv. Chim. Acta 53, 47-53.
26. Wilbur, D. S., Hamlin, D. K., Vessella, R. L., Stray, J. E., Buhler, K. R., Stayton, P. S., Klumb, L. A., Pathare, P. M., and Weerawarna, S. A. (1996) Antibody fragments in tumor pretargeting. Evaluation of biotinylated Fab' colocalization with recombinant streptavidin and avidin. Bioconjugate Chem. 7, 689-702.
27. Lowe, P. A. (1981) Synthesis of sulfonium salts. The chemistry of the sulfonium group: part 1 (Stirling, C. J. M., Ed.) pp 267-312, Chapter 11, John Wiley & Sons, Chichester-New York-Brisbane-Toronto.
28. Gutsche, C. D., and Pasto, D. J. (1975) Fundamentals of Organic Chemistry, pp 600-647, Chapter 21, Prentice-Hall, Inc., NJ.